Firstly, apologies, this is long and probably dull. N/c just in case.
I've been close to a girl a few years younger than me since childhood as our mothers were friends. We're both now mid-20s. Since being a teenager she's had mental health issues and I've been there for her through multiple suicide attempts, drug addictions and overdoses, domestic violence and an abortion. I'd normally go to pick her up, talk to her late at night on the phone, have her to stay, lend her money, take her on weekends away, and so on. She doesn't get much family support. She's fundamentally a very lovely person and I enjoy her company.
In Sept 2011 she moved to my city to start a uni course, and I barely heard from her, far less than before she moved closer (I contacted her a few times suggesting we meet up but didn't push it). I was happy for her as she seemed really stable, was in a good relationship and was clearly making lots of friends, but did miss her a bit. Then she came for a dinner party at mine, and I thought we had a good time. Later though it came back to me from multiple sources, and eventually an email from her, that I'd 'really upset her.' The reason was that at the dinner party (though in private, we were in my bedroom) I'd tried - and clearly failed - to say that she used to be a really sweet girl and it'd been sad she was so unhappy when younger, and I was glad she was now happier. She interpreted that as me saying she used to be a better person and now disliked her. That isn't true - but I'd barely saw her or heard from her in months so didn't feel like I knew her as well any more. I replied to her email saying that and heard nothing back.
Recently she's broken up with the lovely boyfriend and has been seeing our mutual friends more so I've bumped into her a couple of times. From her Facebook she seems pretty upset about the break-up and I hate to think of her being sad without support (she became close to his family). Should I try to extend another olive branch and offer my support/friendship again? Or should I not bother?